Pyridine → Benzamide, N-(3-methyl-2-pyridyl)-

HRID 427215Notes

Reaction equation

HRID 427215 reaction equation
[NH2:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[C:9](Cl)(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.N1C=CC=CC=1>C(Cl)(Cl)Cl>[C:10]1([C:9]2[NH:1][C:2]3[C:7]([CH:8]=2)=[CH:6][CH:5]=[CH:4][N:3]=3)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[C:9]([NH:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][N:3]=1)(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 153472-Amino-3-methylpyridine

Product 2

HCID 90211Benzamide, N-(3-methyl-2-pyridyl)-HCID 6066822-Phenyl-1H-pyrrolo(2,3-b)pyridine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2-phenyl-7-azaindole was prepared in two steps. First, 2-amino-3-picoline was reacted with benzoyl chloride in chloroform in the presence of pyridine to produce 2-benzamido-3-picoline in 33% yield. Second, pyrolysis of 2-benzamido-3-picoline in N-methylaniline in the presence of NaH at 280° C. was performed to produce 2-phenyl-7-azaindole (FIG. 18) in 58% yield. This compound was characterized by NMR spectroscopy.

Sources & evidence

ORD record
ord-3d6d695c26c949799f6b6c52983e589d
Source dataset
uspto-grants-2001_11
Patent number
US06312835B1

Reaction notes

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